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The second from the left is my paternal grandmother, Audrey O'Connor. While the colorized version is certainly well done, the loving cup is not silver, but copper. The engraved loving cup is proudly sitting on my bookcase.

I took the contestants as being (left to right) Gibbs, O'Connor, Buckley and Fleishman. No. 3's outfit looks like a natural for being in red, white, and blue (Buckley's colors), and No. 1's hat looks like an attempt at the Statue of Liberty's crown.

This photo would be great in color: blue and orange?
Based on the descriptions, the ordering in the photo (left-to-right) is:
Dot Buckley, Audrey O'Connor, Muriel Gibbs, Grace Fleishman.

Washington Post, Jul 27, 1919

Galaxy of Beauty Parades at the Beach

Comely Damsels in Scant Attire Win Prizes for Their Appearance

While more than 5,000 persons clambered to each other's shoulders and to the roofs of nearby buildings to view the Annette Kellermanns at the first annual beach parade at the Tidal basin yesterday afternoon. Mrs. Audrey O'Connor, 620 Maryland Avenue southwest, was proclaimed by the judges as Washington's most beautiful girl in a bathing suit. Mrs. O'Conner wore a blue and orange jumper, blue cap and orange tights. Miss Dot Buckley, 1250 Tenth street northwest, received honorable mention in the contest. her suit was a creation in red, white and blue.

First prize in the costume contest was awarded to Mrs. Grace Fleishman, 5 Iowa circle, who wore a white silk suit, with black and white border and a white silk hat. Miss Muriel Gibbs, costumed as Miss Liberty in stars and stripes, received honorable mention. Silver loving cups were awarded to the winners of both the beauty and costume contests.

Following the parade of the score or more of the beauties between the cheering crowds of bathing beach fans, the former faced half a dozen movie machines and a battery of press cameras. Later one of the winners obligingly did a modified "shimmy dance" for the movie men.

Shorpy.com | History in HD is a vintage photo archive featuring thousands of high-definition images from the 1850s to 1960s. (Available as fine-art prints from the Shorpy Archive.) The site is named after Shorpy Higginbotham, a teenage coal miner who lived 100 years ago.